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| Names | |
|---|---|
| IUPAC name 1-[2-(β-D-Glucopyranosyloxy)-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one | |
| Systematic IUPAC name 1-(2,4-Dihydroxy-6-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-3-(4-hydroxyphenyl)propan-1-one | |
| Other names Isosalipurposide | |
| Identifiers | |
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3D model (JSmol) | |
| ChEBI | |
| ChEMBL | |
| ChemSpider |
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| ECHA InfoCard | 100.000.443 |
| UNII | |
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| Properties | |
| C21H24O10 | |
| Molar mass | 436.413 g·mol−1 |
| Appearance | White solid |
| Melting point | 106 to 109 °C (223 to 228 °F; 379 to 382 K) |
| Boiling point | 200 °C (392 °F; 473 K) decomposition |
| water, low MW alcohols | |
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). | |
Phlorizin is aglucoside ofphloretin, adihydrochalcone. A white solid, samples often appear yellowing to impurities. It is of sweet taste and contains four molecules ofwater in the crystal. It is poorly soluble inether and cold water, but soluble inethanol and hot water. Upon prolonged exposure to aqueous solutions phlorizinhydrolyzes to phloretin and glucose.[1]
Phlorizin is found primarily in unripeMalus (apple)[2] root bark ofapple,[3] and trace amounts have been found in strawberry.[4] InMalus, it is most abundant in vegetative tissues (such as leaves and bark) and seeds. Closely related species, such aspear (Pyrus communis),cherry, and otherfruit trees in theRosaceae do not contain phlorizin.[5] Phlorizin is a phytochemical that belongs to the class ofpolyphenols. In natural sources, it may occur with other polyphenols such asquercetin,catechin,epicatechin,procyanidins, andrutin.
Phlorizin is an inhibitor ofSGLT1 andSGLT2 because it competes withD-glucose for binding to the carrier; this action reducesrenalglucose transport, lowering the amount of glucose in the blood.[6][7] Phlorizin was studied as a potential pharmaceutical treatment fortype 2 diabetes, but has since been superseded by more selective and more promising syntheticanalogs, such asempagliflozin,canagliflozin anddapagliflozin.[8] Phlorizin is not an effective drug because when orally consumed, it is nearly entirely converted into phloretin by hydrolytic enzymes in the small intestine.[9][10]
Dihydrochalcones and theirglycosides | |
|---|---|
| Dihydrochalcones: | |
| Dihydrochalconeglycosides: | |
